HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 1'-[(Tert-butoxycarbonyl)methyl]-6-chloro-4'-(3-chlorophenyl)-2'-(1-ethyl-propenyl)-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | tert-Butyl bromoacetate | HCID 79177 | — |
| Reactant | 6-Chloro-4'-(3-chloro-phenyl)-2'-(1-ethyl-propenyl)-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane | HCID 77580071 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 1'-[(Tert-butoxycarbonyl)methyl]-6-chloro-4'-(3-chlorophenyl)-2'-(1-ethyl-propenyl)-2,3-dihydro-2,6'-dioxo spiro[indole-3,3'-piperidine] 1-methoxyethyl trimethylsilane | HCID 77579612 | 37% |
Reaction Steps
In a manner similar to the method described in example 55c, racemic (2′R,3R,4′S)-6-chloro-4′-(3-chloro-phenyl)-2′-(1-ethyl-propenyl)-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane (1.6 g, 2.8 mmol) prepared in example 81a was reacted with bromo-acetic acid tert-butyl ester and cesium carbonate in N,N-dimethylformamide to give racemic (2′R,3R,4′S)-1′-[(tert-butoxycarbonyl)methyl]-6-chloro-4′-(3-chlorophenyl)-2′-(1-ethyl-propenyl)-2,3-dihydro-2,6′-dioxospiro[indole-3,3′-piperidine]-1-methoxyethyl trimethylsilane as a white foam (Yield 0.7 g, 37%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07495007B2 |
| Source dataset | uspto-grants-2009_02 |
| ORD ID | ord-8f3ded05b25f4b99991437438b62b1c0 |
| Source note | uspto-grants-2009_02 |